Derek Sivers - Finding Paths Less Traveled, Taking Giant Leaps, and Picking the Right “Game of Life”

Brought to you by Allbirds incredibly comfortable shoes allbirds.com/, Wealthfront high-yield savings account wealthfront.com/tim, and Shopify global commerce platform providing tools to start, grow, market, and manage a retail business shopify.com/tim
Resources from this episode: tim.blog/2023/04/21/derek-siv...
Derek Sivers is an author of philosophy and entrepreneurship, known for his surprising, quotable insights and pithy, succinct writing style. He is a former musician, programmer, TED speaker, and circus clown, who sold his first company, CDBaby for $22 million and gave all the money to charity.
Derek’s books (How to Live, Hell Yeah or No, Your Music and People, Anything You Want) and newest projects are at his website: sive.rs. His upcoming book is Useful Not True.
Please enjoy!
00:00 Start
00:58 The Derek Sivers School of Enough.
5:33 Scuba diving in Iceland.
10:24 Categories we apply to ourselves and others.
17:15 Derek’s people compass.
22:59 How to secure your tech independence.
59:39 The un-optimized life.
1:11:21 The meaning of Derek’s upcoming book, Useful Not True.
1:28:10 The problem with moral relativism and other -isms.
1:47:21 Giant leaps.
1:56:55 Finding and asking mentors for help.
2:05:20 Games.
2:09:36 The wisdom of quitting when you’re ahead.
2:14:38 Why would Derek - never in need of external validation - seek fame?
2:18:24 What makes Derek so darned interesting?
2:21:00 Has Derek always been a satisficer?
2:30:06 Living on the edge case.
2:34:12 The real question behind “What would you tell your younger self?”
2:39:30 Giving directions in Antarctica.
2:40:31 How do you teach an 11-year-old to act like a 16-year-old?
2:45:04 Parting thoughts.
P.S. To follow the exact step-by-step “Tech Independence” instructions from Derek, please visit sive.rs/ti.
Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 900 million downloads and been selected for “Best of Apple Podcasts” three years running.
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Brought to you by Allbirds incredibly comfortable shoes allbirds.com/, Wealthfront high-yield savings account wealthfront.com/tim, and Shopify global commerce platform providing tools to start, grow, market, and manage a retail business shopify.com/tim

[@sapienspace8814]

Those were touching tears at the end, I wonder if Derek has read "Myth of Normal". I really enjoyed the chat about Minimalism @ 2:26:56 as I'm feeling the suffering of being stuffed (reminds me of a book I got from New Zealand called "Stuffocation"). Willington is a beautiful area. Thank you for sharing!

[@Vexedart]

Enjoyed this one, thanks guys. Such a long gap between the first podcast with Derek and this one. Can definitely sense the evolution of maturity and comfort levels both individually and how you interact with each other. Hope another follow up will come sooner than later.

[@kenwebale5228]

​@@sapienspace8814 😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊

[@mihaelapucko3336]

What a delightful conversation! Derek emanates such positivity and happiness. The positive chemistry between you two is palpable, transcending even through the screens.

[@mackmcd]

This man is a national treasure. Just as Derek finds the most personal value from connecting with other people, anyone fortunate enough to have stumbled upon him in one form or another is richer for it.

[@synja]

Nicely said, however it to scratch

[@spo0ny2k]

He's esoteric foreplay for da ears

[@Mike-lu1pt]

funny you would call him national treasure cuz he renounced his US citizenship

[@mackmcd]

@@Mike-lu1pt I didn't specify which nation. He's a treasure to whichever nation he calls home.

[@lisar.2549]

I could not agree more!

[@Daniel-vl8zm]

I've been listening to other podcasts and haven't picked up a Tim ferriss podcast in a while. My god. He really is the GOAT of podcast hosting. So elite. No one else is as good at letting their guests go on a tangent, then go onto multiple other topics, then come back to the original question and close the loop. Incredible stuff. Helps that Derek is also my absolute favourite interviewee. I wish for you two to get together and do this more for us!

[@chassafrass]

This is one of my favorite episodes! Informative, Entertaining, I laughed, I smiled, I held my breath, I wondered what in the world y'all were talking about and took a deep dive in the google.

[@Zdrokalex]

One of the sweetest and deepest conversations on Tim's podcast. Love this one even more than previous with Derek. Thank you, guys. You are really kinda role models

[@engineeredaf1920]

Derek is my all-time favorite guest. The hell yeah or no episode was life changing since it started me on my self improvement journey.

[@archit8892]

Could you pls share the link of this podcast

[@sindreandersen9114]

Books mentioned (maybe I missed some!) How To Get Rich - Felix Dennis Genghis Khan and the Making of the Modern World - Jack Weatherford How to Stop Worrying and Start Living - Dale Carnegie Paradox of Choice - Barry Schwartz Josh Waitzkin - The Art of Learning 4 Hour Work Week - Tim Ferriss ("His book is trash!") Stumbling On Happiness - Dan Gilbert The How of Happiness: A New Approach to Getting the Life You Want - Sonja Lyubomirsky A Guide to the Good Life: The Ancient Art of Stoic Joy - William B. Irvine

[@wabdih]

I always find myself going back to the art of learning on long walks. Love that book so much so my ears perked up when they mentioned Josh in the last 30 mins. I think I originally got the recommendation from Tim as well in the past.

[@justynarybicka2063]

Thanks! 😊

[@barbdowns1]

This may have been my favorite interview you’ve ever done! Thank you both for a really great podcast episode ❤

[@noaheye3428]

I have way too many "favorite" Tim Ferris Show episodes and this definitely qualifies but then again, the Gul Dolen episode was also a favorite and that goes back a whole 2 episodes!

[@trezr2d2]

yeah he's great

[@Malabarismo]

This is probably my favorite podcast ever. I'm really thankful for the existence of both of you. Reading the 4-hour workweek when I was 15 contributed a lot to set my vision on working full digital and ended up being a huge motor of motivation for me to create this youtube channel with +700 videos about juggling and circus. It changed my life forever because I knew it was possible when deciding to drop out business college to go full time Malabarize-se. Discovered Derek's books and blog because of Tim's interview many years ago and was just hooked. I read probably all the blog posts and books and often recommend his books to friends. Derek really inspires me to be a better human being and hell yeah or no is a framework for decision making that is always on my mind. I love the fact that there are no unnecessary words in his writings If I answered the question of who were my mentors (even them not knowing about it) it would be you two. When I created my TedX talk I remember watching Derek's one 2 or 3 times to think about structure and to look for inspiration. When Tim shared a link I sent on twitter in 5-bullet friday newsletter I remember how happy I was about contributing with it even if just a little bit. Thank you so much for everything you do. For being a source of inspiration in the world. You inspire me a lot to be better everyday 😊 If you ever come to Brazil and want to learn 5 ball juggling (or just have a good chat) drop me a message Keep it up Cheers

[@shrajaldubey7201]

I Loved it so much

[@MP-mr8rj]

To be honest, the last 10 minutes of this podcast hit me like a train! As a father of 2 boys that weight of trying to be a good father is unbelievable! And he’s right, the stakes are SO HIGH!❤ Do your best guys!

[@tom_shooter]

What an amazing human being. Thank you Derek and Tim 🙏

[@simplylive2466]

It made me smile to see how much you diss preppers/prepping, then spend an hour talking about doing things to not be dependent on others and having control/privacy over your own things.... which is just what prepping is all about for most/all preppers

[@Mic.Knowledge]

Damn. What another classic. Love both you guys.

[@brendonla]

Derek was my roommate in Astoria, Queens for about 3 years: although he didn't know me from Adam, he rented a room in his railroad apartment to me because we had a mutual connection/friend (a young woman who worked in his office at the time who also happened to be the daughter of one of my mom's best friends). I always admired his ability to focus on what matters in his life while pursuing his professional goals and dreams with very little compromise while always being friendly and genuine in his interactions. His success since those days, including building and selling CD Baby, doesn't surprise me: that's what happens when people put in the necessary work and focus. Always glad to follow his progress and be stimulated by his ideas. (Jealous as hell though that he gets to live in Wellington, New Zealand....)

[@brendonla]

Also good point from Derek: don't be so reliant on cloud (clown?) services or you could loose all your precious data/photos. And Wordpress is notorious for having security vulnerabilities (though in fairness they address them quickly and there are security plugins like Word Fence to protect your WP instance/site; Derek's point about WP being more than most folks need is true though....)

[@kygo]

Tim, I loved this episode... I think it would be great if you did more "Tim with friends" casual style episodes like this, just like the random shows with Kevin, where you sit down and have an in person chat with a friend or popular repeat guests who aren't trying to sell anything. Watching you in these episodes you look like you enjoy it more too, so would give you an excuse to travel to see them, have a drink etc etc...

[@kevinsamways1776]

Damn. That was just plain ol' fantastic! Love the depth you two have together. And you got my eyes leaking about parenthood. Best gift ever. Thank you!

[@aibochan1764]

Derek’s book Anything You Want is the 2nd best book I’ve read after 4HWW and I re-read it all the time. Highly, highly recommend it.

[@coal.sparks]

I'm not crying along with Derek. It's something in my eye.

[@MikeStillUK]

Listened to this all on audio yesterday now coming back to watch it on video. Special bond and great conversation. I’m here for it.

[@georgeb8637]

1:12:22 - skepticism framework 1:13:00 - 1. Nothing is objectively true 2. Beliefs are placebo 3. Rules and norms are arbitrary 4. Refuse ideology accept ideas individually 1:19:53 - you can believe for 3 minutes or the rest of your life, you will find evidence to support anything you choose to believe 1:36:15 - all or nothing thinking 1:46:00 - once you decided what you want to believe - stack up evidence on to that 1:50:09 - best option is the option that gives you most options 1:56:21 - you don’t have to do anything - but there will be consequences (like not paying taxes) 1:56:40 - value system is growth -simplifies decision making 1:57:28 - I write a really good description of my dilemma 2:04:00 - Situation , assumptions, here what I tired, followed by super specific questions 2:16:59 - success based on what you achieve based on what you set out to do 2:44:11 - raising children right - passing generosity of spirit for generations

[@kev_999]

To Derek: you’re a real one. Thanks for responding to my emails with candor and respect. I wish more people thought the way you do. I could go on but there’s too many examples and this comment would turn into a novel.

[@beateewing8939]

Two forces of nature and two of my favorite people joined in a legendary podcast for almost 3 hours. It doesn't get much better than that. Thank you both; this was incredible stuff.

[@ryandury]

Wow, Tim's take at 14:00 is so on point.Such a good followup to what Derek was talking about. Because labels, or fortune and misfortune can be unpredictable, they can be both a miscalculation when thinking of others, and an unstable identity to hold yourself to as well.

[@seeksustainablejapan]

Such a great talk between you two - the takeaway for me was about mentors you've never met and may not even be real people - love that! As another of your many listeners who has walked away from a successful career to find more meaningful work and living with a better sense of "what is enough" I appreciate this discussion and the many tangents and parallels and inspirations of this discussion!

[@nahushkanitkar8194]

22:59 reminder to self this is what i saved this for.

[@sheerluck4284]

The episodes with Derek are the only ones I listen multiple times. Genuine and lots of insights.

[@HowardARoark]

Towards the end when Derek was in tears on thinking about the critical importance of parenting, you can see how much he cares about that role and how much he recognizes its value. In short Derek is doing God's work there, that's one way to look at it. That goodness of spirit will pass down through the generations, and certainly Derek's spirit will positively influence a great many people's for a long time to come, mine included.

[@0xMN]

So setting up your own server and services and exposing it to the internet , without a firewall (since dedicated servers dont usually have that) is more secure than using a cloud service which is investing heavily in security? Not to mention sh**ting you in the foot with rsync (you should really know how it works)? In my option that is really bad advice. Its only a matter of time until your system gets hacked because you just used the default configuration of a service or forgot to install all security patches. If you are interested in learning the details, go for it. For all regular people, my recommendation is: use secure passwords and multi factor authentication and make regular local backups of your cloud data.

[@Suiterags]

Where else can you find a conversation about email platforms end with tears expressing love for humanity. Thank you ❤

[@ranplan]

He’s still my favorite person/mentor that doesn’t know I exist (well, he did email me after I ordered books from his website). And the person I often tell others to check out. Always excited to read his writing, and of course the rare chance to hear a Derek/Tim convo, especially with video. Inspiring, motivating, entertaining, and everything I hoped/knew it would be. Thank you both, for being my invisible mentors. 🙌🏼

[@realfreedom8932]

THE BEST INTERVIEW, HANDS DOWN, MORE FUN IN INTERVIEWS

[@Susanrogers-pt9mf6hx1w]

Derek is a delight. Honestly the best podcast - finally I find people who have an issue with the cloud and offer alternatives across multiple countries. Thank you from Sydney Oz

[@viybzcontact]

Wow. I’m speechless. Crying. And so happy I got to listen to this. Tim called it, the prep work makes all the difference. You covered so much. Thanks for the generational quote at the end. One of the most incredible conversations I’ve had the pleasure of listening to..thanks gentleman 🖤⚡️

[@JohnHill]

Yes! I have a compilation of quotes from previous podcasts with Derek I frequent 👊

[@tubo1812]

can you share please?

[@dermobbing-ratgeber5166]

@@tubo1812 2:43:20

[@davesteckler]

I have many derekisms that permeate my life

[@antoniomercurio8996]

Holy potatoes - I literally saw the decor of the house and the tree's out the window and thought 'wow, that looks like New Zealand' . TIm and Derek ! Come round for a cup of tea and a tim tam!

[@adamsribz]

This is one of my favorite persons I've ever not had the opportunity of meeting, after hearing your first conversations with him years ago. ☺ I've since learned programming and started a new career. It's always wonderful to hear you two chat!

[@mariyam-sham]

Such a special episode. I LOVE how much fun you are having with each other, while still talking about very valuable topics. Your long friendship definitely adds up to how jovial and relaxed this episode is. My favorite episode for sure!

[@KiaOrion]

one of my favorites from BOTH of y'all. have heard so many from each of you, but your chemistry together was so special to eavesdrop on.

[@cinthyaverasteguieffel8896]

..Thank you SOO much Tim & Derek!

[@Angelblive]

Glad I finally got around to listening to this! Love Derek's work!

[@kevinolega1]

So excited to watch this. Been following the both of you for years. The tools and techniques you both shared changed my life.

[@AllieCatails]

You two are such a fantastic combo of intel, passion, and life experience. Thank you. Love from the Mile High City!

[@garrett3338]

Loved this one! Derek has a great manner of speaking and explaining his thoughts. I really appreciate the video format as well.

[@mathematikexplained6144]

There are many points to elaborate/highlight, but I take this one: If you are in Antarctica every direction you take, leads basically north.

[@DanielFellerFinance]

Wow so cool you two met up in New Zealand on your trip here. 😊

[@thatbusinesstrainer1414]

Simply an amazing episode. Thank you both. You have no idea how much you both have helped me over the years.

[@FemOnlineDance]

Watching these two charismatic personalities interact was an absolute joy, and I found myself completely engrossed in the conversation. Derek Sivers is a truly inspirational figure, and I was fascinated by his insights on creativity, leadership, and personal growth. Meanwhile, Tim Ferriss's interviewing skills are simply unparalleled, and he always manages to bring out the best in his guests. 😀I found this podcast to be a truly inspiring and enlightening experience, and I'm so grateful that it brought me so much joy. I hope that others will also find it to be a valuable resource for pursuing their own goals and aspirations.❤💃

[@metodux]

As someone who has decided to move outside of the states and optimize for location and do "work" my way, I identify here. That very real moment towards the end there and the value of doing parenting right got me right in the feels. The stakes really are that high. Thank you for sharing so vulnerably, Derek.

[@TineTheLoveForLifeFoundation]

This was a conversation i did not want to end. Like being in a precious space with a close friend felt very nutured and reminded of conversations i had with close friends before in time Thanks from my heart

[@RyanEssonYoung]

Setting up your own email server is very complicated, and even if you get everything right a lot of other mail clients still won't be able to contact you... I wish there was a better solution!

[@pranabkumarbora10]

Teared up seeing Derek cry. I love this guy so much. Thank you for this episode, Tim.

[@tubo1812]

time?

[@spo0ny2k]

Slippery sneaky but pertinent ballbag Sivers

[@MarianneHMiettinen]

What a ride and experience of thought provokes. Thank you. This pod just changed my state from anxious to calm. Loved the mentions of Finland too, Greetings from here :)

[@HowardARoark]

Fascinating interview. Sivers is very smart. As a programmer myself I really appreciate his ideas about decentralization. I wonder what he makes of Bitcoin. That was where my journey lead me. I first came across Sivers back around 2010 on a PHP forum and bought one of his books. His philosophy is very interesting. In a world of endless conspiracy he certainly looks like one of the good guys. He knows those big tech companies are not our buddies. I love his punk rock DIY attitude, so refreshing.

[@lisar.2549]

He is way ahead of his time. Brilliant!

[@Marcella_Diane]

Loved this, didn’t want it to end. Loved the reminder of the maximizer, I had read that book but didn’t implement like Derek did, now I’m working on finding place to relocate and move and it helped me. Loved the mentor pre-prep work too.

[@KitaroWaga]

I think it was Derek Siver or Josh Waitzkins Interviews that hooked me to Tim’s podcast. I so much enjoyed this episode. It was like meeting an old friend.

[@victormesserschmidt]

Another great talk with Derek, what a wonderful guy. Cheers to You Two!

[@CJRewired]

I loved this. Friends on tangents! Cohesiveness multiplied. I have to listen again to look up all your references. Cheers

[@menlo7256]

Such a beautiful conversation. Learned a ton from you both over the years when you guys first aired your very first episodes. Keeps geeting better. Your perspectives in life expanded so much over the last 7 years it's amazing to see. Can't wait to tune in to your next recorded chat! cheers from the PH! 🍻🇵🇭

[@sambarryofficial]

This interview has changed my life. Especially learning about the book by Felix Dennis. I respect your work and appreciate what you do Tim! Your work constantly upgrades my mindset.

[@NikoSadlowski]

He’s so wrong about panic attacks. Glad that he took this important lesson. ❤

[@loriegoeser1258]

Thank you for this wonderful, intriguing, thought provoking, and so inspiring discussion on how our inter connection is important!! Thank you both for sharing your gifts with the world!

[@DylanSigleyDropServicing]

Tea & Whisky, will have to try it.

[@moniquefrench]

Great episode, in so many ways. Very .... human conversation ❤

[@gabriel_augustob]

Was waiting for the video! Cheers from Brazil!

[@MP-mr8rj]

Pretty special episode! Definitely in the saved folder! Thanks Tim, and Derek!😍

[@jzen1455]

As someone with a strong affinity for minimalism but also struggle with analysis paralysis, I can't wait to listen to the enitre of the interview.

[@korban007]

appericate first of all the production with good mics and some video. Just something to add, the compression is a touch too aggressive and doesn’t give a natural ambiance in between pauses. Maybe you prefer it like this but for me took away the connection with our great speaker. Thanks for all you do Tim!

[@ZiggyCrane]

Two of my favorite authors in same podcast? Thank you so much, Tim!

[@yzerman6362]

This is the best surprise ever! I just emailed Derek last week since I'd been listening to all the old episodes of his podcast appearances. Can't believe there's finally a new one with him, and on video to boot! Love this new format, Tim

[@timurboltaev8688]

Great listen. Thank you.

[@wickedhyperstyler]

`How to secure your tech independence` was great. Wouldn't have expected that from the episode title, but it came as a pleasant surprise. I wanted to do sth like that for years, but never dared to start that project, although I'm a programmer myself. Thanks for the inspiration and helping hand to Derek!

[@deokyeopkim7720]

Absolutely beautiful

[@tristannewman3437]

Good interview Tim and Derek!

[@hunt.mp4]

So powerful. The comment on examining these “extreme cases”almost feels like the other side of a coin to a previous conversation, where he mentions school curriculum being “organized around the lowest common denominator”, or something along those lines. I’m gonna have to sit with that for a while!

[@themakuachronicles]

Wow I think you just defined the fundamental philosophy behind spiritual science… beliefs are placebos ❤❤❤❤

[@nuskiii8998]

I feel derek is living is up to his last absolutely amazing podcast he had, I constantly think of all the quotes from his podcast, naval say he can't do a sequel to his last interview, love derek

[@bastehaus7708]

Danke!

[@darrenhartigan3033]

Love the happy, nervous energy at the beginning!, I'm gonna stay!! 😅

[@PartyAtFarlows]

That's the way to see London. After ending up wandering the streets of Mayfair, ended up in an underground club filled with Armenians who didn't really speak English well (and I certainly didn't speak theirs)...until Living on A Prayer came on. Suddenly, everyone spoke Bon Jovi and we had one of the best nights ever!

[@bharat5194]

Huge fan of Derek! Thanks for this conversation

[@Finite8614]

So good. Love Derek, love Tim

[@vincentd333]

Great episode!

[@ryanayler7924]

I can listen to this man tell a story about how the paint is drying on the wall

[@MsSylvana63]

Outstanding content, much appreciated ✨🙏🏽✨

[@TrickerDK8]

You guys are the best. Thanks for three hours of amazing company 😊

[@MarkWordie]

Loved this interview - that scotch must be good!!

[@damonm4156]

Thats cool Derek moved to wellington did you do a public talk whilst you were here Tim

[@generate.collective3796]

Umph go power - Derek Sivers ... I appreciate creative word usage 😄

[@cag1]

Good one 🙌🏼

[@chazvegas_]

This is so good. Specifically, I am so thankful to learn about freedom from the cloud or clowns as I will now call it. Thank you!

[@chiefmcconnell]

Objectified... its also mentioned in the 4HC. Objectified: Smart Design OXO grips story 2:31:56

[@lisar.2549]

LOVE you guys! I hate Sam H. though. I won’t even write his full name. This conversation was awesome! Thanks.

[@wandermama]

ahhh derek!!! 🤗🤗🤗🤗

[@rajivshrestha3726]

Best interview ever

[@xelliose]

It's great to see men cry! It's just a release of emotions, not necessarily "sadness"

[@Scoobylife]

He certainly should create a class how to do this!

[@adulion]

I listened to this podcast already but i came back to watch it as derek is so expressive visually. Great guest and great fun podcast

[@paulas6928]

Without a doubt, my favorite of your interviews thus far. 👏👏👏